Who Is Justin Theroux, Really?

As the actor and screenwriter (and Jennifer Aniston's other half) verges on becoming HBO's new main attraction, Willa Paskin encounters a true Hollywood insider with a heart of gold and a brain to match. Just don't call him politically correct.

Black jeans. Black T-shirt. Black boots. Black hair. Black stubble. Two small black tattoos on the left wrist. A thin black leather strap around the right one. When Justin Theroux saunters into a café in Lower Manhattan he meets every expectation of what Justin Theroux, the tabloids' favorite inscrutable outsider, should be like. Then, in all the ways that can't be captured in a TMZ still, he confounds them. With a flash of a warm, gleaming smile and an energetic handshake, Theroux crashes into a chair and starts firing away: Is this table okay? (He's concerned.) The oatmeal here is really good. (He'd like me to know.) Should he have a third cup of coffee? (He wonders aloud.) What would I like to talk about? (He's up for anything.) In five seconds flat, the brooder has emerged as a conscientious chatterbox.

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So what's with the well-documented tough-guy getup? (I ask.) "Whenever I put on a colored thing I feel like I'm in a costume," he says lightly. "Like when I put on a gray shirt." Then I tell him that I'm going to ask about Aniston. He smiles, and replies cheerfully, "You can try!" He doesn't crack, but he is surprisingly Zen about the subject.

Theroux landed a starring role in America's longest-running tabloid soap opera three years ago when he began dating Jennifer Aniston, with whom he costarred in the 2012 comedy Wanderlust. Based on his macho-punk, postmetrosexual (but still exceedingly well-groomed) style, his motorcycle, his refusal to smile for the paparazzi, and the gossip industry's own dedication to presenting Aniston as an underdog, the tabloids have cast Theroux as the withholding, taciturn man who constantly denies America's ever-beleaguered sweetheart whatever it is she really wants—a wedding one week, a baby the next. But it shouldn't come as a surprise that Theroux has no interest in playing the Ken doll role to the tabs' fantasy Barbie. At 42, he is a singular Hollywood creature in his own right: For the past 20 years, he's been a character actor, albeit an unusually handsome one, capable of toggling between comedy and drama, film and TV, as comfortable playing serious and eerie in David Lynch's Mulholland Drive and Inland Empire as he is channeling self-important buffoons in such com-edic farces as Wanderlust (in which he stole scene after scene as the bong-hitting, guitar-playing leader of a free-love commune) and 2011's fantasy send-up Your Highness, and lightening up as Carrie Bradshaw's main squeeze of the week on Sex in the City (twice, actually, as two different characters). Meanwhile, he's become a preeminent screenwriter of blockbusters with a comedic bent: Theroux cowrote 2008's action comedy Tropic Thunder, which made $188 million worldwide and earned Robert Downey Jr. an Oscar nomination for playing a character in blackface. He also wrote 2010's Iron Man 2 (which took in $624 million) and cowrote Tom Cruise's 2012 big-budget hair-metal spoof, Rock of Ages.

This month, Theroux will take on his first (professional) role as a leading man, as the star of HBO's brutal and heartbreaking new drama The Leftovers, based on the novel by Tom Perrotta, which is being adapted for television by Lost creator Damon Lindelof. The series begins one morning in October, in a present-day suburb, when 2 percent of the world's population vanishes with no explanation. Theroux plays Kevin Garvey, a bereaved, angry father and the sheriff of a small town upended by all this loss, a man whose own family has scattered and shattered in the aftermath. The Leftovers has a central mystery—what happened, and why?—but it plays as a study in grief, with all the heaviness and sorrow that suggests. "It's a gut punch, this show," Theroux says. "I'm not comparing it to genuinely tragic events, but throughout our lives, someone will leave. There's usually an explanation for it, but the way that people are affected is deep. Grief is deep. Everyone mourns or panics in a different way, and the show is like a pinball machine of dysfunction. It's a sad show to make, but it's punctuated—I should say perforated—with little bursts of light, which I think are essential."

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It's also the kind of tortured and meaty part in an existentially high-minded series that has turned working actors like James Gandolfini and Jon Hamm into household names, and Theroux grabs onto it with an intelligent tenacity that makes you wonder what took Hollywood so long to lift him out of the supporting cast and try him as a front man. "I've been in a fair amount of scenes with a fair amount of men at this point, and there are very few performers who can hold that wounded male energy, be very masculine and strong and also in need," says actress Amy Brenneman, who plays Theroux's estranged wife on the show. "Some dudes just feel like, 'If I'm showing that, then I'm not strong.' People have their hang-ups. But Justin's able to bring all his masculinity and muscularity and beauty and also be very, very vulnerable." Lindelof puts it this way: "He's the guy, and he's wearing it very well."

Theroux has long been at home among Hollywood's biggest names offscreen, however. There's Aniston, of course, but he also counts a cadre of very funny—and very powerful—people as friends, including Ben Stiller, Jason Bateman, and Will Arnett (who calls him during our lunch to figure out a time for them to hang and, when Theroux tells him he's currently in the middle of an ELLE interview, says he recommends "an open-toed shoe and a little clutch"). Then there's the band of comic actors he works with and writes for that includes Stiller, Downey, Danny McBride, and Paul Rudd. Another such friend, the actress and comedian Amy Sedaris, who met Theroux through mutual friend Philip Seymour Hoffman, describes him in a way that is eerily similar to his description of The Leftovers. "Justin's got this dark side—he'll go there," she says, "but more than anyone I've ever met, he just really does blossom with sunshine." Then, crushing any remaining shard of suspected biker-dude bravado: "Justin is like a girlfriend. He'll do girly things with you: He'll tan, he'll put your makeup on for you, he gives great advice."

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Theroux was born in Washington, DC; his father was a lawyer, his mother a journalist and novelist, and his uncle is the novelist and travel writer Paul Theroux. As a kid, Theroux, who was diagnosed with ADHD, didn't exactly thrive in school. ("I wasn't particularly good at anything academic," he says. "Math is still a magic trick to me. Acting was the thing I gravitated to, because I enjoyed it.") He bounced from middle school to middle school before landing at a boarding school in Williamstown, Massachusetts, where he and his classmates would perform Shakespeare and Ionesco for local schoolkids. Theroux graduated from Bennington College in 1993 with majors in visual arts and drama and headed straight to New York City. He got an apartment on the Bowery and bartended on Bleecker Street while doing his own art and painting murals in lofts and at clubs, as well as acting. After he got some attention for his Off-Broadway parts, director Mary Harron cast him in his first movie, the 1996 Valerie Solanas biopic I Shot Andy Warhol. Theroux's first decent paycheck and what he refers to as his "I can go to the dentist, I can go to the grocery store" money came the following year via an Alyssa Milano vehicle so forgettable it was marketed twice, first under the title Below Utopia and then as Body Count.

In 1997, Theroux met Ben Stiller through Stiller's then girlfriend, Jeanne Tripplehorn, with whom Theroux costarred in a Broadway production of Chekov's The Three Sisters, and in Stiller found a mentor and a compadre who encouraged his fledgling screenplays. The two began developing an action-comedy script that eventually became Tropic Thunder. The bromance has been hot and heavy ever since, and if all goes according to plan, Theroux will write and direct Zoolander 2.

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"Acting," Theroux says, "is a job of permission. Someone has to give you permission to do it. But I have started to be like, 'I only want to do things that I want to do,' and writing has afforded me the luxury. Being handed a well-thought-out, beautifully written piece of ma-terial that I don't have to affect at all, except for performing it.… It's a joy to read something I have no desire whatsoever to change." Writing, on the other hand? "Writing is hard."

Though the movies Theroux writes aren't lacking in explosions or dirty jokes, they're challenging—funny, confrontational, and commercial, all at the same time. Tropic Thunder is a spoof of both Platoon and the world of Hollywood in general. In its most memorable scene, Downey's character, a method actor who has undergone "pigmentation alteration" to play a black sergeant, explains to Stiller's character that an actor should never go "full retard" if he wants to win an Oscar. The controversial scene embodies Theroux's priorities: "There's a certain point where political correctness becomes extremely conservative and it skews to a point where it becomes humorless," he says. Instead, he cares that the point is incisive, the joke is funny, the words precise. "You have to be sure of what your target is, who the joke is on," he continues. "I was so saddened that people were offended by the full-r-word scene, because we worked really hard making sure that joke was aimed at Hollywood and actors portraying mentally challenged people. I remember being so bummed out. They literally picketed us. It was like, 'Really? Satire is allowed to do this!' "

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Theroux's aversion to political correctness runs so deep that he is working on an animated series examining the theme—a long-germinating project modeled on All in the Family, but with the Archie Bunker character as a liberal instead of a conservative. "When was the last time you were super offended? I might be like, 'That's the dumbest thing I've ever heard!' Or, 'It's not my thing,' or, 'It was a stupid joke.' But there's such a sensitivity now. Political correctness has become really insidious."

Yes, to Justin Theroux, political correctness is even more bothersome than the paparazzi. "My life changed a lot," he says with a shrug, regarding his entry into a relationship with Aniston and, with it, a paparazzi state. "More people are like, 'Hey, man!' And I don't think that's from my role in John Adams. But it only changed as much as I engaged with it, and I learned very quickly: Don't ever engage with it. Just JKL. It was a learning curve, but it wasn't as traumatic as you might expect. It's just annoying. Occasionally you'll get a stewardess congratulating you, on, I don't know, whatever, some three-headed baby we just had."

As befits a writer, Theroux's biggest beef with the celebrity press is the paucity of their storytelling skills. "I can't get over how terrible the narrative is, just how poorly written it is," he says. "It's worse than a telenovela. It's so dramatic. Like, 'They're broken up, they're together, they're storming out, storming in, rushing out, rushing in.' They make every celebrity look like a schizophrenic." But sitting across from him, it seems Theroux's head couldn't be screwed on straighter. He has a more nuanced narrative to live.

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